Whitman sets before us the ideal: “Behold I do not give lectures or a little charity, When I give I give myself.” This is to say that charitable giving, done right, is intrinsically and intensely personal. When we give away our money- the same might be said for our time- something of ourselves invariably comes along for the ride. What we give almost always comes bundled with hopes, expectations, fears and conditions, however inarticulate they may be. The same can be said for those on the receiving end as well. Agency colors action. There is no way around it.
Not all those hopes, expectations, fears and conditions are fair or warranted. Not all of our giving is virtuous. This way of putting things sounds a bit old fashioned-- indeed, the language of 'virtue' harkens back to the ancient Greeks, for whom it named knack for processing feelings and desires appropriately, in ways that ultimately led one to make the kinds of decisions that contribute a good, happy life. Aristotle developed a theory-- popular to this day-- that saw virtue in the cultivation of a middle state between two extremes, one in which a quality in question is deficient and another in which it is excessive.
When it comes to the giving of money, the virtue most in demand we call generosity. In Aristotelian terms, generosity names the middle state avoiding the extremes of being 'stingy,' on the one hand, and 'wasteful,' on the other, with one's wealth. It describes the quality-- not quantity-- of one's giving, which is to say that how much one gives means little, since Aristotle suggests that those of modest means as well as the very wealthy can be equally generous. What matters, rather, is that you "give to the right people, the right amounts, at the right time, and [...] with pleasure or without pain.”
One often gives with mixed motives. One may practice philanthropy less out of generosity that out of guilt, to right a wrong, with a desire for prestige or reward, or with the expectation of influence. giving may be virtuous in one sense but not in another (Plato would likely disagree, but this is another matter). To give virtuously you have to have a clear sense of not only why you are giving but also how those to whom you are giving understand the situation.
This is why, at Remington Weld, before we begin to discuss "strategy" and what you hope to achieve with your philanthropy, you should be prepared to endure a series of more or less Socratic interrogations designed to help you more clearly discern who you really are, who you think you are, and, perhaps, who you are trying to become through the practice of philanthropy.
Is this a painful process? You bet! It requires a deep, sustained commitment to honesty and self-reflection. But, it is the necessary pain that one must go through in order to emerge as a confident, strategic and truly generous grantmaker capable of giving "with pleasure" as Aristotle would have it.